2-Phenyl-4-quinolones와 Methyl Iodide의 친핵반응에 의한 유도체의 합성

• 영문명: Nucleophilic Reaction of 2-Phenyl-4-quinolones with Methyl Iodide and Preparation of Its Derivatives
• 발행기관: 대한약학회
• 저자명: 오미정(Mi-Jung Oh) 박명숙(Myung-Sook Park)
• 간행물 정보: 『약학회지』제52권 제6호 (2008년), 514~519쪽, 전체 6쪽
• 주제분류: 의약학 > 기타의약학
• 파일형태: PDF
• 발행일자: 2008.12.31

영문 초록

We developed a convenient synthetic route to 3-alkylated 2-phenyl-4-quinolone derivatives (4a-h and 5a-c), which were expected to retain antitumor activity. A series of 2,3-dihydro-2-hydroxy-2-phenyl-4-quinolones (3a-h) was synthesized through dehydration, dealcoholation and hydration using acid-catalyzed one-pot reaction from anilines and ethyl benzoylacetates. 3-Methyl (or 3,3-dimethyl)-2-phenyl-4-quinolone derivatives 4 and 5 were synthesized from 3a-h through the methylation using methyl iodide. Formation of quinolone nucleus was undertaken with p-toluenesulfonic acid (p-TSA) at 90~110℃ in toluene for 3~7.5 hr over the Dean-Stark apparatus. The key intermediates in these preparations are β-ketoesters 2a-h, which can be readily obtained from the corresponding anilines 1a-e by reaction with ethyl bezoylacetates.

키워드

3-alkyl-2-phenyl-4-quinolone C-methylation monomethylated quinolones dimethylated quinolones